Thionyl Chloride → 2-(Chloromethyl)-1-methylbenzimidazole

HRID 279567

Reaktionsgleichung

Reaktionsgleichung von HRID 279567
O[CH2:2][C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=1.S(Cl)([Cl:15])=O>>[Cl:15][CH2:2][C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=1

Komponenten

3

Edukt 2

HCID 24386Thionyl ChlorideHCID 344177(1-methyl-1H-1,3-benzodiazol-2-yl)methanol

Produkt 1

HCID 2480442-(Chloromethyl)-1-methylbenzimidazoleAusbeute 36 %

Versuchsvorschrift

A solution of 2-hydroxymethyl-1-methylbenzimidazole (1.1 g, 6.7 mmol) in thionyl chloride (10 ml) was stirred at ambient temperature for 15 minutes and then heated at reflux for 15 minutes. The volatiles were removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 2-chloromethyl-1-methylbenzimidazole (506 mg, 36%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 15 minutes
  3. customThe volatiles were removed by evaporation
  4. customthe residue purified by column chromatography
  5. washeluting with methylene chloride/methanol (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-d8c3115e42f34c5791ca6054fb4ab195
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06362336B1

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